2-Aminophenol → 2-(4-Chloro-2-fluoronitrobenzen-5-yl)benzoxazole

HRID 74293노트

반응식

HRID 74293 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1O.CCN=C=NCCCN(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([C:4]2[O:6][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]=2)=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([F:11])[CH:10]=1

참가 물질

7

반응물 4

HCID 58012-AminophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

생성물 1

HCID 674987962-(4-Chloro-2-fluoronitrobenzen-5-yl)benzoxazole수율 26.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

2-Chloro-4-fluoro-5-nitrobenzoic acid (4.00 g, 18.2 mmol), 2-aminophenol (2.09 g, 20.1 mmol), CHCl3 (80 mL), and WSC (3.84 g, 20.0 mmol) were added together and stirred at room temperature for 2 hours. Water was added, and this was extracted with chloroform/acetone (3:1). After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. To a toluene (80 mL) solution of the solid obtained was added p-toluenesulfonic acid monohydrate (0.18 g, 1.8 mmol), and this was heated to reflux for 40 hours. After the reaction solution was concentrated, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (1.40 g, 26% yield) as yellowish-brown crystals.

후처리

  1. extractionthis was extracted with chloroform/acetone (3:1)
  2. customAfter the organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate, it
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customTo a toluene (80 mL) solution of the solid obtained
  7. temperaturethis was heated
  8. temperatureto reflux for 40 hours
  9. concentrationAfter the reaction solution was concentrated
  10. additionwater was added
  11. filtrationthe precipitated crystals were filtered
  12. washafter being washed with water
  13. customwere dried

출처 및 근거

ORD 기록
ord-d22aabb4074e46d7825cf02f64005d7d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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